cas 2210-79-9, 2-[(2-Methylphenoxy)methyl]oxirane

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Synthesis and bio-evaluation of a novel selective butyrylcholinesterase inhibitor discovered through structure-based virtual screening
In recent years, butyrylcholinesterase (BChE) has gradually gained worldwide interests as a novel target for treating Alzheimer's disease (AD). Here, two pharmacophore models were generated using Schr?dinger suite and used to virtually screen ChemDiv database, from which three hits were obtained. Among them, 2513–4169 displayed the highest inhibitory activity and selectivity against BChE (eeAChE IC50 > 10 μM, eqBChE IC50 = 3.73 ± 1.90 μM). Molecular dynamic (MD) simulation validated the binding pattern of 2513–4169 in BChE, and it could form a various of receptor-ligand interactions with adjacent residues. In vitro cytotoxicity assay proved the safety of 2513–4169 on diverse neural cell lines. Moreover, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay performed on SH-SY5Y cells proved the neuroprotective effect of 2513–4169 against toxic Aβ1–42. In vivo behavioral study further confirmed the great efficacy of 2513–4169 on reversing Aβ1–42-induced cognitive impairment of mice and clearing the toxic Aβ1–42 in brains. Moreover, 2513–4169 was proved to be able to cross blood-brain barrier (BBB) through a parallel artificial membrane permeation assay of BBB (PAMPA-BBB). Taken together, 2513–4169 is a promising lead compound for future optimization to discover anti-AD treating agents.
Chen, Yao,Chen, Ying,Feng, Feng,Jiao, Mengxia,Li, Qi,Liu, Wenyuan,Lu, Weixuan,Sun, Haopeng,Wang, Yuanyuan,Xing, Shuaishuai,Xiong, Baichen
p. 1352 - 1364
(2020/11/19)

Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives
Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).
Sarojini, Perumal,Jeyachandran, Malaichamy,Sriram, Dharmarajan,Ranganathan, Palraj,Gandhimathi
(2021/02/26)

Design, synthesis and biological evaluation of novel desloratadine derivatives with anti-inflammatory and H1 antagonize activities
To improve the anti-inflammatory activity of desloratadine, we designed and synthesized a series of novel desloratadine derivatives. All compounds were evaluated for their anti-inflammatory and H1 antagonistic activities. Among them, compound 2c showed the strongest H1 antagonistic and anti-inflammatory activity. It also exhibited promising pharmacokinetic profiles and low toxicity. All these results suggest that compound 2c as a novel anti-allergic agent is worthy of further investigation.
Li, Feng,Xu, Qinlong,Zhu, Qihua,Chu, Zhaoxing,Lin, Gaofeng,Mo, Jiajia,Zhao, Yan,Li, Jiaming,He, Guangwei,Xu, Yungen
(2019/11/03)

A facile and efficient method for synthesis of β-iodocarboxylates from terminal epoxides
A facile and efficient method has been developed for synthesis of β-iodocarboxylates in the presences of Ph3P/I2. Starting from epoxides, a series of β-iodocarboxylate compounds can be directly obtained in toluene media with excellent yields. Moreover, the method was successfully applied for the late-stage modification of natural products, such as isosteviol and vincamine derivatives, achieving the corresponding β-iodocarboxylates in good yields.
Zhu, Ye-Fu,Wei, Bo-Le,Wang, Wen-Qiong,Xuan, Li-Jiang
supporting information

(2019/11/26)

NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b] [1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes
(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.
Dong, Jun,Xu, Jiaxi
p. 9037 - 9044
(2018/06/08)

Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols
An efficient synthesis of β-amino alcohols from a variety of epoxides and primary unbranched amines in the absence of any catalyst in high yields and regioselectivities is reported. A variety of polar mixed solvent systems allow for the selective formation of secondary amino alcohols over tertiary amino alcohols. The reaction scope extends to a wide variety of aromatic and aliphatic substituted epoxides and primary amines bearing complex functionality.
Lizza, Joseph R.,Moura-Letts, Gustavo
supporting information
p. 1231 - 1242
(2017/03/11)

THERAPEUTIC COMPOUNDS
The present invention relates to therapeutic compounds useful for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia). The compounds have the structural formula I shown below: wherein Q, X, p, R1, q, R3 and R4 are as defined herein. The present invention also relates to pharmaceutical compositions comprising the compounds defined herein, the use of these compositions for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia), and to processes for the preparation of the pharmaceutical compositions defined herein.
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Paragraph 00118; 00124

(2015/02/02)

Analysis of β-amino alcohols as inhibitors of the potential anti-tubercular target N-acetyltransferase
The synthesis and inhibitory potencies of a novel series of β-amino alcohols, based on the hit-compound 3-[3′-(4″-cyclopent-2?- en-1?-ylphenoxy)-2′-hydroxypropyl]-5,5 dimethylimidazolidine-2,4- dione as specific inhibitors of mycobacterial N-acetyltransferase (NAT) enzymes are reported. Effects of synthesised compounds on growth of Mycobacterium tuberculosis have been determined.
Fullam, Elizabeth,Abuhammad, Areej,Wilson, David L.,Anderton, Matthew C.,Davies, Steve G.,Russell, Angela J.,Sim, Edith
supporting information; experimental part
p. 1185 - 1190
(2011/04/16)

Synthesis of aryloxyacetaldehydes and N-(aryloxyethyl)cyclohexanamine hydrochloroides
Oxidation of 2-(aryloxymethyl)oxiranes with periodic acid gave a series of aryloxyacetaldehydes which reacted with cyclohexylamine in THF, and subsequent reduction of Schiff bases thus obtained with sodium tetrahydridoborate resulted in the formation of the corresponding secondary amines which were isolated and characterized as hydrochlorides.
Shapenova,Belyatskii,Panicheva
experimental part
p. 1017 - 1020
(2010/10/21)

Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism
Some 3-aryloxy-1,2-epoxypropanes, interesting as potential synthons in β-adrenergic receptor antagonists preparation, were obtained in excellent yields (65-96% within 2-17 min) by microwave activation (monomode system) using solid-liquid solvent-free phase transfer catalysis (PTC). The best results for the O-alkylation of some phenols with epichlorohydrin were obtained using TBAB and NaOH/K2CO3 (1:4 mol/mol) as phase transfer catalyst and more acceptable basic system, respectively. These new procedure is compared with classical methods. Significant specific microwave effect (non-purely thermal) was evidenced in all cases. They were discussed in terms of reaction medium and mechanism, taking into account the variations in polarity of the systems.
Pchelka, Beata K.,Loupy, Andre,Petit, Alain
p. 10968 - 10979
(2007/10/03)

Synthesis, anorexigenic activity and QSAR of substituted aryloxypropanolamines
Substituted aryloxypropanolamines (6-20) were synthesized and evaluated for their anorexigenic activity. Among them 4-cyanoaryloxy (7), 2-methylaryloxy (9), 2-methoxyl aryloxy (10), 4-acetamidoaryloxy (15), 4-bromoaryloxy (16) and 4-ethylaminoaryloxy (20) exhibited potent anorexigenic activity. According to QSAR studies, the electronic parameter 'σ' plays an important role in describing the variance in activity. Birkhaeuser Boston 2004.
Srivastava, Shipra,Bhandari, Kalpana,Shankar, Girija,Singh,Saxena, Anil K.
p. 631 - 642
(2007/10/03)

1-Alkylthio-3-aryloxypropan-2-ols: Synthesis and enantiomer separation by lipase-catalyzed transesterification
The optically active (R)- and (S)-1-alkylthio-3-aryloxypropan-2-ols were prepared in the reaction of the appropriate arylglycidyl ethers and alkyl thiols followed by lipase-catalyzed transesterification. The effect of aryl and alkyl substituents, the enzyme preparation as well as the reaction conditions have been compared in terms of enantiomeric excess of the obtained acetate and the unreacted alcohol.
Wielechowska, Monika,Plenkiewicz, Jan
p. 3203 - 3210
(2007/10/03)

Resolution of racemic 3-aryloxy-1-nitrooxypropan-2-ols by lipase-catalyzed enantioselective acetylation
Both (R)- and (S)-enantiomers of 3-aryloxy-1-nitrooxypropan-2-ols (R)-(-)-1, (S)-(+)-2 were prepared in high enantiomeric excess by lipase from Pseudomonas cepacia (Amano PS) or Pseudomonas fluorescens (Amano AK)-catalyzed acetylation of racemic alcohols 1a-g with vinyl acetate in n-hexane at 4 or 22°C. The enantioselectivity of this transformation was dependent on the substitution pattern of the aryl ring with E-values ranging from 31 to 111.
Pchelka, Beata Krystyna,Loupy, Andre,Plenkiewicz, Jan,Petit, Alain,Blanco, Luis
p. 2109 - 2119
(2007/10/03)

Synthesis of [14C]-Labelled glycidyl and glycerol ethers of aliphatic and aromatic alcohols.
The synthesis of [14C]-labelled glycidyl ethers and the corresponding glycerol ethers is described for the monofunctional compounds 1-dodecanol and ortho-cresol and the bifunctional compounds 4,4'-dihydroxy-3,3',5,5'-tetramethyl biphenyl and 1,6-hexanediol. The synthesis is based on reaction between the alcohol and [U-14C]-epichlorohydrin. The aromatic compounds have been converted to the corresponding glycidyl ethers by using sodium hydroxide and the aliphatic compounds by using tin(IV) chloride as a catalyst. Thus radio-labelled glycidyl ethers were obtained in yields between 50-80, with a chemical purity of > 92 and a radiochemical purity of > 95 by HPLC. The specific activities of the glycidyl ethers were approximately 0.2 mCi/mmol for the monofunctional compounds and approximately 0.4 mCi/mmol for the bifunctional compounds.
Van Elburg,Ormskerk,De Kloe,Boogaard
p. 147 - 167
(2007/10/03)

Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation
Kinetic resolution of racemic 1-azido-3-aryloxy-2-propanols 1a-g was performed using supported lipase of Candida antarctica-B (Novozym() SP 435) in toluene at 4°C with isopropenyl acetate as the acyl donor to afford the optically active (S)-alcohols 2a-g and their corresponding (R)-acetates 3a-g with E values from 56 to 72. Copyright (C) 2000 Elsevier Science Ltd.
Pchelka, Beata Krystyna,Loupy, Andre,Plenkiewicz, Jan,Blanco, Luis
p. 2719 - 2732
(2007/10/03)

Dermal penetration and metabolism of five glycidyl ethers in human, rat and mouse skin
1. Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. 2. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine th apparent permeability constants, lag times and metabolic profiles. 3. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. 4. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 12GE 12GE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. 7. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.
Boogaard,Denneman,Van Sittert
p. 469 - 483
(2007/10/03)

Metabolic inactivation of five glycidyl ethers in lung and liver of humans, rats and mice in vitro
1. Some glycidyl ethers (GE) have been shown to be direct mutagens in short-term in vitro tests and consequently GE are considered to be potentially mutagenic in vivo. However, GE may be metabolically inactivated in the body by two different enzymatic routes: conjugation of the epoxide moiety with the endogenous tripeptide glutathione (GSH) catalysed by glutathione S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by epoxide hydrolase (EH). 2. The metabolic inactivation of five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), has been studied in subcellular fractions of human, C3H mouse and F344 rat liver and lung. 3. All GE were chemically very stable and resistant to aqueous hydrolysis, but were rapidly hydrolysed by EH in cytosolic and microsomal fractions of liver and lung. The aromatic GE were very good substrates for EH. In general, microsomal EH is more efficient than cytosolic EH in hydrolysis of GE, and human microsomes are more efficient than rodent microsomes. 4. The more water-soluble GE, o-CGE and HDDGE, were good substrates for GST whereas the more lipophilic GE, YX4000 and C12GE, were poor substrates for GST. In general, rodents are more efficient in GSH conjugation of GE than humans. 5. In general, the epoxide groups of YX4000 are the most and those of HDDGE the least efficiently inactivated of the five GE under study. For the other three GE no general trend was observed: the relative efficiency of inactivation varied with organ and species. 6. The large variation in metabolism observed with five representative GE indicate that GE have variable individual properties and should not be considered as a single, homogenous class of compounds.
Boogaard,De Kloe,Bierau,Kuiken,Borkulo,VanSittert
p. 485 - 502
(2007/10/03)

Microwave enhanced synthesis of epoxypropoxyphenols
Phenols were condensed with epichlorohydrin under microwave irradiation. Dramatic reduction in reaction time was observed with excellent yields.
Khadilkar, Bhushan M.,Bendale, Pravin M.
p. 2051 - 2056
(2007/10/03)

A novel method for synthesis of aryl glycidyl ethers
A solid-liquid phase-transfer catalytic method for the synthesis of aryl glycidyl ethers has been described, and the factors affecting the reaction yield have been examined.
Liu,Chen,Cao,Li
p. 833 - 838
(2007/10/02)

REACTION OF o-CRESOL WITH EPICHLORHYDRIN IN THE PRESENCE OF ONIUM SALTS
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Kobzev, S. P.,Simonov, M.A.,Romantsevich, A. M.,Mironenko, N. I.,Opeida, I. A.
p. 366 - 370
(2007/10/02)

Formation of Optically Active Aryloxyacetaldehyde Cyanohydrin Acetates with the Aid of a Microorganism
Microorganisms that hydrolyze the one enantiomer of dl-phenoxyacetaldehyde cyanohydrin acetate were screened, and Bacillus coagulans isolated from soil was found to be the best.This bacterium was applied to the asymmetric hydrolysis of other aryloxyacetaldehyde derivatives to give satisfactory results.The effect of adding dimethyl sulfoxide to the medium is also described.
Ohta, Hiromichi,Miyamae, Yoshitaka,Tsuchihashi, Gen-ichi
p. 215 - 222
(2007/10/02)

Design and synthesis of a series of combined vasodilator/β-adrenoceptor antagonists based on 6-arylpyridazinones
A series of new 6-[4-[[(aryloxy)acyl]amino]phenyl]-4,5-dihydropyridazinones have been synthesized and evaluated as combined vasodilator/β-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances, improved duration of action. All of the compounds were vasodilators, but the 5-methylpyridazinone derivatives showed consistently greater antihypertensive activity than their 5-H lower homologues. Further detailed pharmacological investigations led to the selection of 6-[4-[3-[[2-hydroxy-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propyl]amino ]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (4t) (SK&F 95018) as a development candidate.
Slater,Howson,Swayne,Taylor,Reavill
p. 345 - 351
(2007/10/02)

Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
Novel compounds of the general formula STR1 and the pharmaceutically acceptable esters and acid addition salts thereof, wherein: R1, R2, R3, R4 and R5 are each independently hydrogen, lower alkyl, lower alkoxy, cyano, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, N-optionally substituted alkylamido, except that when R1 is methyl, R4 is not methyl; or R2 and R3 together form --OCH2 O--; R6, R7, R8, R9 and R10 are each independently hydrogen, lower acyl, aminocarbonylmethyl, cyano, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, di-lower alkyl amino; or R6 and R7 together form --CH=CH--CH=CH--; R7 and R8 together form --OCH2 O--; R11 and R12 are each independently hydrogen or lower alkyl; and W is oxygen or sulfur. These cardioselective compounds have calcium entry blockade properties and therefore are useful in therapy in the treatment of cardiovascular diseases, including arrhythmias, variant and exercise induced angina and myocardial infarction.
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(2008/06/13)

COMPOUNDS AND METHOD FOR TREATMENT OR PROPHYLAXIS OF CARDIAC DISOREDRS
A short-acting β-blocking compound of the formula STR1 wherein Ar may be substituted or unsubstituted aromatic, Y may be a straight or branched carbon chain or aralkyl, R may be lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, and x is an integer from 1 to about 3; or a pharmaceutically acceptable salt thereof.
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(2008/06/13)

Ultra-Short-Acting β-Adrenergic Receptor Blocking Agents. 3. Ethylenediamine Derivatives of (Aryloxy)propanolamines Having Esters on the Aryl Function
Various ethylenediamine derivatives have been incorporated into the nitrogen substituent of certain short-acting (aryloxy)propanolamine systems that contain esters on their aryl functions.Although several of these compounds showed durations of action comparable to their prototypes, most of the nitrogen substituents significantly prolonged the duration of β-adrenergic blockade.Similarly, while one of the compounds showed appreciable cardioselectivity in vitro, generally, little enhancement of cardioselectivity was obtained.A brief discussion of structure-activity relationships observed for the ethylenediamine derivatives is presented.
Erhardt, Paul W.,Woo, Chi M.,Matier, William L.,Gorczynski, Richard J.,Anderson, William G.
p. 1109 - 1112
(2007/10/02)

Preparation of aliphatic/aromatic ethers
Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:
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(2008/06/13)

THIENYL AND BENZOTHIENYL-TERTIARY BUTYLAMINOPHENOXYPROPANOLS
Substituted 1-phenoxy-3-(thienyl-tert.-butylamino)-2-propanols and related 3-benzothienyl compounds are selective β-receptor blocking agents. Preferred compounds bear an ortho-substituent on the phenoxy ring.
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(2008/06/13)

Antihypertensive indole derivatives of phenoxypropanolamines with β-adrenergic receptor antagonist and vasodilating activity
A series of 25 aryloxypropanolamines containing the 3-indolyl-tert-butyl[i.e., 1,1-dimethyl-2-(1H-indol-3-yl)ethyl] or substituted 3-indolyl-tert-butyl moiety as the N substituent is reported. These compounds have been tested for antihypertensive activity in spontaneously hypertensive rats (SHR), β-adrenergic receptor antagonist action in conscious normotensive rats, vasodilating activity in ganglion-blocked rats with blood pressure maintained by angiotensin II infusion, and for intrinsic sympathomimetic action (ISA) in reserpinized rats. Some of the compounds exhibit antihypertensive activity in combination with β-adrenergic receptor antagonist and vasodilating action. The structure-activity relationships in these tests are discussed.
Kreighbaum,Matier,Dennis,Minielli,Deitchman,Perhach Jr.,Comer
p. 285 - 289
(2007/10/02)